PL126256B1 - - Google Patents

Description

**** - * * • * •! | Inventor. Authorized by the patent: BASF Aktiengesellschaft, Ludwigshafen (Federal Republic of Germany) Herbicide. The subject of the invention is a valuable herbicide containing new substituted pyridazones as active substances. It is known that l-phenyl is known from the German patent specification No. 1,197,676 -4,5-dimethoxy-6-pyridazone has a broad herbicidal action and can therefore be used as a total herbicide with the simultaneous destruction of crops. This active substance destroys plants both in pre-emergence application and in the treatment of leaves. Moreover, Belgian patent specification 728 164 describes 1m-trifluoromethylphenyl-4,5-dimethoxy-6-pyridazone with similar herbicidal properties. the use of sodium salt of 2-chloro-4-trifluoromethylphenyl-3'-carboxy-4'-nitrophenylether is known as a herbicide, e.g. German patent DOS No. 2 311638. It was found that good herbicidal and unexpected crop tolerance is shown by substituted pyridazones of the general formula I, in which R2 is a halogen atom, such as chlorine or bromine, or an alkoxy group with 1-3 carbon atoms, such as methoxy, R * denotes amino groups , alkylamino, dialkylamino, alkoxyamino or alkylalkoxyamino having 1 to 3 carbon atoms in each case in the alkyl or alkoxy group, the alkyl groups being the same or different, further 10 R 1 represents a halogen atom, such as chlorine or bromine, an alkoxy group with 1-3 carbon atoms, such as a methoxy group, a trimethylene imino group, or an amine group acylated by a group of the formula C1CH2C (0) or CH3COOCH, C (O), X represents a substituted phenoxy group of the general formula II, where R *, R4 and R5 each independently represent a hydrogen or halogen atom, such as chlorine or bromine, nitro, cyano, carboxyl, alkyl, such as methyl, haloalkyl, such as methyl, haloalkyl, such as trifluoromethyl, alkoxy, such as methoxy, haloalkoxy, alkyl mercaptan, haloalkyl mercaptan, alkylsulfinyl or alkylsufonyl, each containing 1 or 4 halogen atoms, and Y represents carbon atoms such as chlorine, haloalkyl, cyano or nitro. In the general formula 1 R 1 is, for example, fluoro, chloro, bromo or iodo, methoxy, ethoxy, propoxy and R 1 is for example Example: amine, methylamino, ethylamino, dimethylamino, dithylamino, methylethylamino, methoxyamino, methylmethoxyamino, chlorine or bromine, methoxy, ethoxy, propoxylate ClCHaCfOJNH- or CH O, COOCH, C - or a trimethyleneimine group. X represents, for example, a substituted phenoxy group of the general formula 3, 4 or 5, where R *, R4 and R5, depending on each other, represent, for example, hydrogen, fluorine, chlorine, bromine or iodine. , nitro, cyano, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl groups. chloromethyl, difluorochloromethyl, 1-chloroethyl, 2-chloroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2,2-trichlorethyl, 2,2,2-trifluoroethyl, 1,1,2,2- tetrafluoroethyl, 1,1.2-trifluoro-2-chloKetlyow: α, 1,1,2,2,2-pentafluoroethyl, methoxyl, ethoxy, n-propoxy, isopropoxy, tert-butoxy, trichloromethoxy. trifluoromethoxy, 1-chloroethoxy, 2-chloroeth-, "xylic, 1-fluoroethoxy, 2-fluoroethoxy, 2,2,2-trichloreoxy, 2,2,2-trifluoroethoxy, 1,2,2-tetrafluoroethoxy" , 1,1,2,2,2-pentafluoroethoxy, methyl mercaptan, ethyl mercaptan, trichloro-methyl mercaptan, trifluoromethyl mercaptan, methylsulfinyl, ethylsufinyl, methylsulfonyl or an ethylsulfonyl group, hydrogen, Y, for example, iodine, iodine or iodine. cyano or nitro group. There are compounds of the general formula I, in which R2 is, for example, a chlorine or bromine atom or a methoxy group, R1 is, for example, an amino, methylamino, dimethylamino, methylmethoxyamino or methoxy group, and X represents a phenoxy group substituted in the 3- or 4-position of the phenyl group by a halogen atom or a haloalkyl group, especially a chlorine atom and a trifluoromethyl group, and Y is a hydrogen atom or a nitro group at the 6-position of the group Pyridazones of the general formula I in which R 1 is not a halogen atom are prepared by reacting a dihalpyridazone of the general formula 6 in which X and Y are as defined above and Hal is a halogen atom, especially chlorine or bromine. , with at least twice the stoichiometric amount of the amine of the general formula HNR3R4, in which R3 or R5 is a hydrogen atom, an alkyl group of 1-3 carbon atoms or an alkoxy group of 1-3 carbon atoms, or a more or less stoichiometric amount in relation to the halogen atom to be reacted - depending on whether one or both halogen atoms are to be reacted - an alkoxide of the general formula MOR5, in which M is a metal cation, especially sodium or potassium, and R5 is an alkyl group of 1-3 atoms With carbon, such as a methyl group, the reactions being true in the presence of an organic solvent at a temperature of 20-150 ° C, under normal or increased pressure, 100-1000 kPa, in a continuous or intermittent manner. and 1- (4 '- (3-trifluoromethylphenoxy) / phenyl-4,5-dichloromethylphenoxy) / phenyl-4,5-dichloromethyl-6-pyridazone and sodium methoxide are used as starting materials, the course of the reaction is shown in scheme 1. The dihalopyridazone of the formula 6 is first dissolved or dispersed in an organic solvent, for example ethanol, and then reacted with an appropriate amount of an alkoxide or amine, which may also be used in the form of an aqueous or alcoholic solution, German Patent DOS No. 25 26 643, DE-PS 12 10 241 and DOS 16 95 840 and US Patent 2 628 181. The reactions are carried out under normal or elevated pressure, for example 0.5-12 hours at a temperature of 20 -150 ° C, in particular 50-120 ° C, continuously or intermittently. The reaction mixture is worked up according to generally used methods. If the final product is solid, it is isolated, for example, by filtration under reduced pressure, if it is dissolved in a solvent, the solvent flows away under reduced pressure, the residue mixed with water and dripped under reduced pressure. The product is purified, for example, by crystallization or by chromatography. The dihalopyrizadines used as starting materials in the general formula 6 are prepared, for example, as follows: Phenylhydrazines of the general formula 7, in which X and Y are as defined above, are reacted with 3-formyl-2-acid , 3-dihaloacrylic of the formula H 2 C-C (Hal) = C (Hal) -CHO, in which Hal is a halogen atom, in particular chlorine or bromine, preferably at room temperature, in the presence of a solvent, e.g. a solution of a mineral acid or a hydrated or anhydrous inert organic solvent such as ethanol which is evaporated after completion of the reaction, and the corresponding dihalacid semicarbazone obtained as a reaction product, for example without isolation, is cyclized to the corresponding compound without isolation. Formula 6 by heating to reflux in glacial acetic acid or acetic anhydride, or by heating in an aqueous mineral acid, for example hydrochloric acid, at 70 ° -100 ° C. or by mixing in concentrated mineral acid, e.g. sulfuric acid, at room temperature (20UC), German DOS Patent Nos. 16 95 830, 25 26 643 and 15 45 595. The process is carried out continuously or batchwise and the mixture is The reaction is worked up by generally used methods. The phenylhydrazines of the general formula VII required as starting materials can be obtained generally by known methods from the corresponding anilines of the general formula VIII, in which X and Y have the above-mentioned meanings, in the usual manner by diazotization 50 and subsequent reduction of the diazonium salt, e.g. - -Weyl, Methoden der organische Chemie, vol. 10/2, page 180, publishing house Georg-ThiemeA Stuttgart 1667. Reactions to the corresponding pyridazone can be carried out without hydrazine isolation, however, a cleaner end product is obtained when phenylhydrazine is isolated in the form of Hydrochlorides. Anilines of the general formula 8 can be obtained in the case of 4-phenoxy-substituted derivatives by known methods, German Patents DOS No. 24 11,320, while the 3-phenoxy-substituted derivatives are known from Liebigs Ann. Chem. 740, 169-179 (1970) or they can be prepared in a known manner. The examples below illustrate the preparation of new compounds of the general formula I, the parts by weight relating to parts by volume as kilogram to liter. Example I. 25.3 parts by weight of 4- (3'-trifluoromethylphenoxy) -aniline dispersed in 230 parts by volume of concentrated hydrochloric acid is diazotized at 0 ° C with 6.9 parts by weight of NaNO 2 in 30 parts volume of water and then reduces 45 parts by weight of SnCl2 to 4- (3'-trifluoromethylphenoxy) -phenylhydrazine hydrochloride. The hydrochloride is dispersed in 400 parts by volume of 2 N hydrochloric acid, 16.7 parts by weight of 3-formyl-2,3-diacrylic acid are added and the mixture is kept at 90 ° C for 1 hour. After cooling, the hydrochloric acid is separated from the organic phase, which is mixed with 160 parts by volume of glacial acetic acid and stirred for 10 minutes under reflux. The reaction mixture is then cooled and water is added. The resulting 1- / 4 '- (3 "-trifluoromethylphenoxy) / - phenyl-4,5-dichloro-6-pyridazone is filtered off under reduced pressure and recrystallized from methanol. Yield 28.9 parts by weight, corresponding to 72% yield theoretical; melting point 115-117 ° C - active ingredient No. 1 Example II.28.7 parts by weight of 3- (2'-chloro-4'-trifluoromethylphenoxy) -aniline are nitrosated with a solution of 7.6 parts by weight NaNO in 50 parts by volume of concentrated sulfuric acid in 200 parts by volume of glacial acetic acid at 10-20 ° C. The diazonium salt solution is reduced directly to the corresponding hydrazine by a solution of 45.5 parts / g of SnCl3 in 31 parts by volume of concentrated Hydrochloric acid. After the addition of 16.7 parts by weight of 3-formyl-2,3-dichloroacrylic acid, the reaction solution is stirred at reflux for 10 minutes, then cooled and 1000 times by volume of water are added. the residue is dissolved in dichloromethane, dried with magnesium sulfate, the solvent is distilled off, and the residue crystallizes by trituration with methanol. This gives 32 parts by weight, corresponding to 74% of theoretical yield, 1- (3 '- (2 "-chloro-4" -trifluoromethylphenoxy) -phenyl-4,5-dichloro-6- pyridazone with a melting point of 89-92 ° C - active substance No. 2. Example III. 20 parts by weight of 1- / 4 '- (3 "- trifluoromethylphenoxy) / - phenyl-4,5-dichloro-6-pyridazone and 4 parts by weight of sodium methoxide in 80 parts by volume of methanol are boiled for 1 hour under reflux The reaction mixture is evaporated to dryness, the residue is mixed with water and filtered under reduced pressure. After recrystallization from methanol, 32 parts by weight are obtained, corresponding to 801% theoretical, l- / 4 '- (3 " -trivoromethylphenoxy) phenyl-4-methoxy-5-chloro-6-pyridazone, m.p. 113-114 ° C. - active ingredient No. 3. 10 parts by weight of 1- (3 '- (2 "- chloro-4'r-trifluoromethylphenoxy) - phenyl-4,5-dichloro-6-pyridazone and 6.3 parts by weight of sodium methoxide in 100 parts by volume of absolute toluene is boiled for 1 hour. The reaction mixture is then filtered hot and the filtrate is evaporated to dryness. The oily residue is triturated with diisopropyl ether and 3.9 parts by weight are obtained by filtration under reduced pressure, corresponding to 3 S ° / theoretical yield, 1- (3 '- (2 "- chloro-4" -trifluoromethylphenoxy) - phenyl-4,5-dimethoxy-6-pyridazone with a melting point of 72-79 ° C - active substance No. 4 10 Example 5 26 parts by weight of 1- / 3 '- <2 "- chloro-4" -trifluoromethylphenoxy) / phenyl-4,5-dichloro-6-pyridazone and 16 parts by weight of methylamine dissolved in 100 parts of the volumetric ethanol together is boiled for 1 hour, then drained hot, concentrated to dry and the residue mixed with water. After filtration under reduced pressure and recrystallization from methanol, 15 parts by weight, i.e. 58% of theory, 1- / 3'- 20 (2 "-chloro-4" -trifluoromethylphenoxy phenyl-4-methylamino-5) are obtained. chloro-6-pyridazone with a melting point of 186-188 ° C - active substance No. 5 Example VI. Solution 20 parts by weight 1- / 3 '- (2 / r-chloro-4' / - trifluoromethylphenoxy) / - phenyl- » 4,5-dichloro-6-pyridazone in 300 parts by volume of glacial acetic acid is nitrated at 0-5 ° C with a mixture of 5.6 parts by weight of nitric acid with a density of 1.40 and 5.9 parts by weight of concentrated acid. sulfuric acid. Stirring for 2 hours at 5 ° C. and adding 1000 parts by weight of water. The precipitate is filtered off under reduced pressure and the residue crystallizes from diisopropyl ether. This gives 13.3 parts by weight, corresponding to 60% of theory 1- / 3 '- (2 * -chloro-4 "-trifluoro-methylphenoxy) / 6'-nistro / -phenyl-4,5-dichloro o-6-pyridazone with a melting point of 128-130 ° C - active ingredient No. 6. Example VII. 15 parts by weight of 1- / 3 '- (2 "- 40 chloro-4" -trifluoromethylphenoxy) -6 / -nitro / -phenyl-4,5-dichloro-6-pyridazone and 200 parts by volume of concentrated ammonia solution are heated for 12 hours at 100.degree. C. in an autoclave under self-pressure. The residue is filtered under reduced pressure, and after recrystallization from methanol, 10 parts by weight are obtained, corresponding to 72% of theoretical yield, M3'- (2 "-chloro-4-trifluoromethylphenoxy) -6, -nitro / phenyl -4-amino-5-chloro-6-pyridazone with a melting point of 227-230 ° C - active substance No. 7 The active substances presented in the table are prepared in a manner corresponding to the examples 1-7. Non-oxy-substituted pyridazones for the growth of desired and undesirable plants is presented by experiments carried out in a greenhouse. Plastic pots with a capacity of 300 cm * were filled with clay sand containing about 0.15% / t of humic substances and a plate was sown. the seeds of the test plants, separately according to the species. Immediately after sowing, the surface of the soil was pre-emergence with the active substances applied pre-emergence by means of finely grinding nozzles, dispersed or emulsified in the water. ie126 256 9 \ \ Table Active substance No. i 8 18 19 20 22 23 24 31 .35 10 12 89 93 91 94 95, »6 97 98 100 101, 102 [103 104 111 112 113 114 115 116 117 118 119 120 121 122 123 | X oci 2-chloro-4-trifluoromethylphenoxy 3-chloro-4-trifluoromethylphenoxy 3-chloro-4-trifluoromethylphenoxy 3-chloro-4-trifluoromethylphenoxy 3-chloro-4-trifluoromethylphenoxy 3-chloro -4-trifluoromethylphenoxy 3-chloro-4-trifluoromethylphenoxy 2,4-dichlorophenoxy 2,4-dichlorophenoxy 2-chloro-4-trifluoromethylphenoxy 3-trifluoromethylphenoxy 3-trifluoromethylphenoxy 3-trifluoromethylphenoxy 4 -chlorophenoxy 4-chlorophenoxy 4-chlorophenoxy 4-chlorophenoxy 4-chlorophenoxy 2-chloro-4-trifluoromethylphenoxy 2-chloro-4-trifluoromethylphenoxy 2-chloro-4-trifluoromethylphenoxy 2-chloro-4-trifluoromethylphenoxy 2-chloro-4-trifluoromethylphenoxy 3-chloro-4-trifluoromethylphenoxy 2,5-dichlorophenoxy 2,5-dichlorophenoxy 3-bromophenoxy "2-bromo-4-chlorophenoxy 2-bromo-4-chlorophenoxy »3,4-dichlorophenoxy» 3-trifluoromethoxy-phenoxy "1 Item X 3 ~ 3 3 4 3 3 4 3 4 4 3 3 4 4 4 4 4 4 4 4 3 3 3 3 3 3 4 4 4 4, 4 4 4 4 4 4 4 4 1 Y 4 "~" HH HHHHHHHHHHHHH 3-CF3 ljn 6-NOz 6-NO2 »i» "H" H "" "H" ii "1" 1 "1 ** 1 R1 5 NH2 Cl Cl OCH3 OCUs OCH8 NH2 Cl OCHs OCH3 N (OCH3) OCH3 NH2 NHCH3 Cl OCH3 OCH3 NHCH3 NH2 OCH8 OCH, NHCH3 N (CH3) 2 NCOCHs) CHj NHCH3 Cl OCH3 Cl OCH * Cl OCH, Cl OCH, 'Cl OCH, Cl OCH, | R2 6 Cl Cl Cl Cl OCH, OCH3 Cl Cl OCH, Ci C1CH, C1CH, Cl Cl Cl Cl OCH3 Cl Cl Cl OCH3 Cl Cl Cl H Cl OCH3 Cl OCH3 Cl OCH, Cl OCH, Cl OCH, Cl OCH, | Temp. Melting point (° C) n ™ Band wavelength in the IR spectrum 7 204-206 C = 0 1670 cm-i ng 1.5883 1.5987 C = 0 1650 cm-i 1.5749 154-158 122-124 126-131 112 —115 78—82 84—85 175—177 131—134 129—131 168—170 98—100 156—158 199—201 179—181 128—131 164—167 155—159 167—171 C = 0 = 1620 cm -i 81—84 98—103 110—113 96—99 128—131 111—115 91—93 100—105 137—142 101—103 84—89 58—63 | 126 256 10 1 1 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 | 144 2 3-tert.-butylphenoxy mp 3-methoxyphenoxy ii 4-chloro-3-methylphenoxy »» 3-methylphenoxy »» 2-chloro-5-methylphenoxy mp 2-chloro-4-bromophenoxy mp 3 -fluorophenoxy i "3-trifluoromethylphenoxy» »tt in 2-chIoro-4-trifluoro-methylphenoxy tt 3 3 4» »» »» n »ii * H u" • i »« fi »» »and 3- C1 "3-CF, if tt 6-NO2 u 5 / Cl OCH, Cl OCH, Cl OCH, Cl OCH, Cl OCH, Cl OCH, Cl OCH, Cl OCH, ci OCH, NHCH, NH-CHt (iso) N (CA) i * 6 Cl OCH, Cl OCH, Cl OCH, ci OCH, Cl OCH, Cl OCH, Cl OCH, ci OCH, Cl OCH, Cl Cl Cl cd. table * 1 76-77. 1.5768 97—101 71—76 160—163 83—86 v 130—132 79—81 88—92 109—112 130—132 138—140 130—133 84—88 105—109 82—69 84—89 75 —82 C = * 0 1620 cm- * 170—176 142—143 | as a spreading agent. With this application method, the application rates of the active compounds were 3.0 kg / hectare. After the application of the active ingredients, the vessels were slightly moistened to encourage germination and growth. The vessels were then covered with translucent plastic film until the plants had grown. This covering resulted in uniform germination of the test plants, as long as they were not damaged by the active substances. In the case of post-emergence treatment, the active substances were applied after the test plants had grown up to a height of 3 to 3, depending on the form of growth. 10 cm. For the post-emergence treatment, either the plants grown directly and in the same pots were used, or the seedlings were first grown separately and transplanted into the test vessels a few days before the treatment. In the post-emergence application, the doses of active substances were 0.25 kg / hectare and 0. 5 kg / hectare. The known active substances were used as comparative agents in the same doses, namely 1-phenyl-4,5-dimethoxy-6-pyridazone (A), 1-m-trifluoromethyl-4, 5-dimethoxy-6-pyridazone (B) and the sodium salt of 2-chloro-4-trifluoromethylphenyl-3'-carboxy-4'-nitrophenylether (C). No foil was used in the post-emergence treatment. The experiments were carried out in a greenhouse, where the species of plants that liked warmth were kept in a warmer area with a temperature of 20-30 ° C, and species of temperate climate in the area with a temperature of 15-25 ° C for 2 to 4 weeks. May hours. During this time, the plants were tended and their responses to individual treatments were assessed on a scale of 0-100, with 0 being no damage or normal emergence, and 100 being no plant emergence or complete destruction of at least the above-ground parts. that the new active substances, in the majority of the post-emergence treatments carried out, show a similar, and even better, herbicidal action against some undesirable species than the known active compound used for comparison. It should be emphasized in particular that the tolerance of the new active substances by crops, especially those of the grass family, is much more favorable. A herbicidal effect has also been observed with pre-emergence application. If certain crops are somewhat sensitive to the active ingredients, it is also possible to use an application technique in which the herbicides are directed by a sprayer so that they do not hit as much as possible. on the leaves of sensitive crops, and reaching the leaves of undesirable plants growing below, or on the soil surface not covered (post directed, lay-by). Due to the good tolerability and versatility of the methods of application, the agent according to the invention can be used to remove undesirable vesicles in a further large number of crops. The dose of active compound used was 0.1-15 kg / hectare and more. The following arable crops, for example, can be used: In order to extend the range of action and obtain a synergistic effect, the new phenoxy-substituted pyridazones can be mixed and applied together between soba and numerous representatives126 256 Botanical name \ "l" ¦ Allium cepa [Ananas comosus Arachis hypogaea r Asparagus officinalis 1 Avena sativa Beta vulgaris spp. altissima Beta vulgaris spp. rapa Beta vulgaris spp. esculenta Brassica napus var. napus Brassica napus var. napobrassica Brassica napus var. rapa Brassica rapa var. silvestris Camellia sinensis Carthamus tinc- torius Catrya illinoinen- l sis Citrus linwm Citrus majdma Citrus reticulata Citrus sinensis. 1 Coffea arabica kcoffea canephora, Coffea liberica) Cucumis melo Cucumis sativus Cynodon dacty- lori Daucus carota / Elaeis guineensis Fragaria vesca Glycine max Gossypium hir- lutum (Gossy¬ pium arbtreum, Gossypium her- baceium, Gossypium her- bace) Helianthus tuberosus Hevea brasiliensus Hordeum vulgare I Polish name 1 ~ r "common onion pineapple peanut asparagus oats r sugar beet. Pasture beet red beet rape rape white beet rape herb bush safflower safflower pecan pecan lemon grapefruit mandarin orange market coffee melon cucumber placzyca 1 garden carrot oilseed wild strawberry soybean cotton sunflower sunflower tuber rubber tree - 1 yielding barley English name | - 3 ~ "onions pineapple i peanutus sugar (grounclnuts) asparagus food beets, red beets rape seed turnips tea plants safflower pecan trees l lemon grapefruits oragne trees coffee plants melons cucumber Bermudagrass in turfs and lawns carrots oil palms strawberries soybeans cotton i sunflowers V 1 rubber plants barley 5 10 15: 20 25 30 35 40 45 50 55 60 • 1 1 Humulus lupulus Ipomoea batatas Juglans regia Lactuca sativa Lens culinaris Linum usitatis- simum Lycopershot lycopersicum Malus spp. Mani escu¬lenta Medicago sativa Mentha piperita Musa spp. Nicotiana taba- -cum (N. rustica) Olea europaea Oryza sativa Panicum milia-ceum Bhaseolus lu- natus Phaseolus mungo Phaseolus vul- garis Pennicetum glaucum Petroselinum cispum spp. tuberosum Picea abies Abies alba Pinus spp. Pisum sativum Prunus avium Prunus domestica Ribes Prunus ducvestis Ribes Prunus domestica Ribes Prunus ducvestis Ribes -crispa Ricinus communis Saccharum offi- cinarum Secale cereale Sesamum indi- cum Solanum tuberosum | - 2 1 hops' common morning glory walnut | global lettuce lentils flax tomato apple cassava alfalfa pepper mint banana tobacco olive rice millet moon beans mungo bean common beans millet pearl parsley spruce white fir white pine pine pea black cherry olive peach candle Pear tree black apple sugar cane sugar cane common rye sesame potato 1 3 1 hop sweet potato walnut trees lettuce lentils flax tomato apple trees cassava alfalfa (lucerne) peppermint banana plants tabacco olive trees fice limabeans 1 mungbeans snapbeans , green beans, dry beans 1 parsley 1 Norway spruce fire pine trees English peas cherry trees plum trees almond trees peach trees pear trees red currants sugar cane rye sesame Irish potato13 126 256 14 1 1 Sorghum bicolor (S. vulgare) Sorghum dobna Spinacia oleracea Theobroma cacao Trifolium pra- tense Triticum aestivum Vaccinum corym- bosum Vaccinium vitis- -idaea Vicia faba Vigna sinensis (V. unguiculata) Vitis vinif era Zea mays 2 giant millet sugar sorghum spinach cocoa tree red clover wheat blueberry blueberry cow bean bean vine corn 3 1 sorghum spinach cacao plants red clover wheat blueberry cranberry tick beans cow peas grapes Indian corn, sweet corn, maize other groups of active substances with a herbicidal or plant growth regulating effect. Mixtures include, for example, diazines, 4H-3 derivatives, i-benzoxazines, 2,6-dinitroanilines, N-phenylcarbamates, thiol carbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinines, uracils, benzofuran derivatives, 1,3-cyclohexanedione derivatives and others. The following is an example of a number of active substances which, together with the active substances according to the invention, give mixtures preferred for the most diverse fields of application. These are: 5-amino-4-chloro-2-phenyl-3 (2H) -pyridazinone, 5-amino-4-bromo-2-phenyl-3 (2H) -pyridazinone, 5-amino-4-chloro-2 -cyclohexyl-3 (2H) -pyridazone, 5-amino-4-bromo-2-cyclohexyl-3 (2H) -pyridazinone, 5-methylamino-4-chloro-2- (3-trifluoromethylphenyl) -3 (2H) -pyridazinone, 5-methylamino-4-chloro-2- (3-ala, p, P-tetrafluoroethoxyphenyl) -3 (2H) -pyridazinone, 5-dimethylamino-4-chloro-2-phenyl -3 (2H) -pyridazinone, 4,5-dimethoxy-2-phenyl-3 (2H) -pyridazinone, 4,5-dimethoxy-2-cyclohexyl-3 (2H) -pyridazinone, 4,5- dimethoxy-2- (3-trifluoromethylphenyl) - 3 (2H) -pyridazinone 5-methoxy-4-chloro-2- (3-trifluoromethylphenyl) - 3 (2H) -pyridazinone, 5-amino-4-bromo-2- ( 3-methylphenyl) -3 (2H) -pyridazinone, 3- (1-methylethyl) -1H-2, 1,3-benzQthiazin-4 (3H) -one 2,2-dioxide, and 2, 3- (1-Methylethyl) -8-chloro-1H-2,1,3-benzothiadiazin-4 (3H) -one 2-dioxide and salts, 3- (1-methylethyl) -8-fluoro 2,2-dioxide -1H-2, l, 3- benzothiadiazin-3 (3H) -one and 3- (l-methylethyl) -8-methyl-lH-2, l, 3-, 2,2-dioxide, salts nzothiadiazin-4 (3H) -one and salts, l-methoxymethyl-3- (l-methylethyl) -2,1,3-benzothiadiazin-4 (3H) -one 2,2-dioxide, l- 2,2-dioxide methoxymethyl-8-chloro-3- (1-methylethyl) -2,1,3-benzothiadiazin-4 (3H) -one, tyloethyl) -2,2-dioxide 1-methoxymethyl-8-fluoro-3- ( 1-methylethyl) - 2, 1, 3-benzothiadiazin-4 (3H) -one, 1-cyano-8-chloro-3- (1-methylethyl) -2,1,3-benzothiadiazines 2,2-dioxide -4 (3H) -one, 2,2-dioxide 1-cyano-8-fluoro-3- (1-methylethyl) -2,1,3-benzothiadiazin -4 (3H) -one, 2,2-dioxide 1 -cyano-8-methyl-3- (1-methylethyl) -2,1, 3-benzothiadiazin-4 (3H) -om 2,2-dioxide 1-cyano-3- (1-methylethyl) -2, 1,3-benzothiadyiazin-4 (3H) -one, 2,2-dioxide 1-azidomethyl-3- (1-methylethyl) -2,1,3-benzothiadiazin-4 (3H) -one, 2,2 - 3- (1-methylethyl) -1H-pyridine- (3,2-e) 2, 1,3-thiadiazin-4-one, N- (3- (N'-phenylcarbamHoxy) -phenyl) ethylcarbamate, N - (3- (N'-3,4-difluonphenylcarbamoyloxy) -phenium and ethyl loH-carbamate, N- (3- (N'-3,4-difluorophenylcarbamoyloxy) -phenyl) -carbamate, N- 3- (4-f methyl luorophenoxycarbonylamino) phenylcarbamate, methyl N-3- (2-methylphenoxycarbonylamino) -phenylcarbamate, methyl N-3- (4-fluorophenoxycarbonylamino) -phenylthiolothiolocarbamate, N-3- (2,4,5-trimethylaminooxycarbonyl) ) - methyl phenylthiolcarbamate, methyl N, N-3- (phenoxycarbonylamino) -phenylthiolcarbamate, p-chlorobenzyl N, N-diethylthiolcarbamate, ethyl N, N-di-n-propylthiolcarbamate, N, N-di-n-propylthiolcarbamate propyl, 2,3-di-chloroallyl N, N-diisopropylthiolcarbamate, 2,3,3-trichloroallyl N, N-diisopropylthiolcarbamate, 3-methyl-5-isoxazolylmethyl N, N-diisopropylthiolcarbamate, 3-methyl-5-isoxazolylmethyl N, N-diisopropylthiolcarbamate -5-isoxazolylmethyl, ethyl N, N-di-sec-butylthiolcarbamate, benzyl N, N-di-sec-butylthiolcarbamate, ethyl N-ethyl-N-cyclohexylthiolcarbamate, N-ethyl-N-bicyclo- 2, Ethyl 21β-heptylthiolcarbamate, 2,3-di-chloroallyl 2,2,4-trimethylazetidine-1-carbothiolate, 2,2,4-trimethylazetidine-1-carbothiolate n-2,3,3-tri-chloroallyl, ethyl hexahydro-1-H-azepine-1-carbothiolate, benzyl 3-methylhexahydro-1H-azepine-1-carbothiolate, 2,3-dimethylhexahydro-1H-azepine-1-carbohydrate - benzyl thiolate, u 15 20 21 30 35 40 48 M 55 6015 126 256 16 ethyl 3-methylhexahydro-1H-azepine-1-carbothiolate, n-propyl N-ethyl-Nn-butylthiol thiolcarbamate, 2-chloroallyl N, N-dimethyldithiocarbamate , Sodium N-methyldihydiocarbamate, sodium trichloroacetate, a, a-dichloropropionate, a, sodium ct-dichloropropionate, sodium a, a, p, O-tetrafluoropropionate, a-methyl-a, p-sodium dichloropropionate, a-chloro Methyl-P- (4-chlorophenyl) -proponate, methyl α, O-dichloro-P-phenylpropionate, benzamidoxyacetic acid, 2,3,5-triiodobenzoic acid and salts, esters and amides, 2,3,6- acid trichlorobenzoic acid * and salts, esters and amides, 2,3,5,6-tetrachlorobenzoic acid and salts, esters and amides, 2-methoxy-3,6-dichlorobenzoic acid and salts, esters and amides, 2-methoxy-3 acid , 5,6-tricobenzoic acid and salts, esters and amide y, 3-amino-2,5,6-trichlorobenzoic acid and salts, esters and amides, O, S-dimethyl tetrachlorothioterephthalate, dimethyl 2,3,5,6-tetrachloroterephthalate, disodium 3,6-endoxohexahydrophthalate, 4-amind-3,5j6-trichloropicolinic acid and ethyl 2-cyano-3- (N-methyl-N-phenyl) aminoacrylate salts, 2- (4- (4- (4) -chlorophenoxy) -phenoxy) -isobu propionate methyl 2- / 4- (2 ', 4'-dichlorophenoxy) -phenoxy) -propionate, 2- / 4- (2'-chloro-4'-trifluoromethylphenoxy) -pheno-2 ^ 4- (4'- Methyl trifluoromethylphenoxy) phenoxy / propionate, sodium xy / propionate, 3- (4- (3 \ 5'-dichloropyridyl-2-oxyHenoxy) - sodium propionate, 2- (N-ben20yl-3l4-dichlorophenylamino) - ethyl propionate, methyl N-2-(N-benzoyl-3-chloro-4-fluoroIenylamino) -propionate, isopropyl 2- (N-benzoyl-3-chloro-4-fluorophenylamino) -propionate, * fe 2-chloro-4-ethylamino-6-isopHipylamin-1,3l5-triazine, 2-chloro-4-ethylamino-6- (amino -? '- propionitrile) - 1,3,5-triazine, 2-chloro-4 -ethylamino-6- (2-methoxypropyl-2-amino) -1,3,5-triazine, 2 -chloro-4-ethylamino-6-butyn-l-yl-α-amino-1,3,5-triazine, 2-chloro-4,6-bis-ethylamino-1,3,5-triazine, 2-chloro -4,6-bis-isopropylamino-1,3,5-triazine, 2-chloro-4-isopropylamino-0-cyclopropylamino-1,3,5-triazine, 2-azido-4-methylamino-6-isopropylamino-1 , 3,5-triazine, 2-methylthio-4-ethylamino-6-isopropylamino-1,3,5-triazine, 4-methylthio-4-ethylammo-6-tert-butylamino-1,3,5-triazine, 2- methylthio-4,6-bis-ethylamino-1,3,5-triazine, 2-methylthio-4,6-bis-isopropylamino-1,3,5-triazine, 2-methoxy-4-ethylamino-6-isopropylamino- 1,3,5-triazine, 2-methylthio-4,6-bis-isopropylamino-1,3,5-triazine, 2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine, 2- methoxy-4,6-bis-ethylamino-1,3,5-triazine, 2-methoxy-4,6-bis-isopropylamino-1,3,5-triazine, 4-amino-6-tert-butyl-3- methylthio-4,5-dihydro-1,2,4-triazin-5-one, 4-amino-6-phenyl-3-methyl-4,5-dihydro-1,2,4-triazin-5-one, 4-isobutylideneamino-6-tert-butyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one,1-methyl-3-cyclohexyl-6-dimethyl amino-1,3,5-triazine-2,4-dione, 3-tert-butyl-5-chloro-6-methyluracil, 3-tert-butyl-5-bromo-6-methyluracil, 3-isopropyl- J-bromo-6-methyl uracil, 3-sec-butyl-5-bromo-6-methyluracil, 3- (2-tetrahydropyranyl) -5-chloro-6-methyluracil, 3- (2-tetrahydropyranyl) -5 , 6-trimethylenuracil, 3-cyclohexyl-5,6-trimethylenuracil, 2-methyl-4- (3V-trifluoromethylphenylMetrahydro-1,2,4-oxadiazine-3,5-dione, 2-methyl-4- (4'-fluorophenyl) -tetrahydro-1,2,4-ex- diazine 3,5-dione, 3-amino-1,2,4-triazole, 1-allyloxy-1- (47-bromophenyl) -2- (r, 2 ', 4 '-triazol-r-yl) -ethane and salts, 1- (4-chlorophenoxy) 3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone, N, N-diallylchloroacetamide, N-isopropyl-2-chloroacetanilide, N- (1-butyn-3-yl) -2-chloroacetanilide, 2-methyl-6-ethyl-N-propargyl-2-chloroacetanilide, 2- methyl-6-ethyl-N-ethoxymethyl-2-chloroacetanilide, 2-methyl-6-ethyl-N- (2-methoxy-1-methylethyl) - 2-chloroacetanilide, 2-methyl-6-ethyl-N- isopropoxycarbonylethyl-2-chloroacetanilide, 2-methyl-6-ethyl-N- (4-methoxy-1-pyrazolylmethyl) -2-chloroacetanilide, 2-methyl-6-ethyl-N- (1-pyrazolylmethyl) -2-chloroacetanilide, 2,6-dimethyl-N- (1-pyrazolylmethyl) ) -2-chloroacetanilide, 2,6-dimethyl-N- (4-methyl-1-pyrazolylmethyl-2-chloroacetanilide, 2,6-dimethyl-N- (4-methyl-1-pyrazolylmethyl) -2-chloroacetanilide , 2,6-dimethyl-N- (11,2,4-triazol-1-ylmethyl) -2-chloroacetanilide, 2,6-dimethyl-N- (3,5-dimethyl-1-pyrazolylmethyl) -2-chloroacetanilide , 2,16-dimethyl-N- (1,3-dioxolan-2-ylmethyl) -2-chloroacetanilide, 2,6-dimethyl-N- (2-methoxyethyl) -2-chlorpacetanilide, α., 6-dimethyl- N- (2-methoxyethyl) -2-chloroacetanilide. 2,6-dimethyl-N-isobutoxymethyl-2-chtoroacetanilide, 2,6-diethyl-N-methoxymethyl-2-chloroacetanilide, 10 15 20 25 30 35 401 45 50 55 9017 126 256 18 2,6-diethyl- Nn-butoxymethyl-2-chloroacetanilide, 2,6-diethyl-N-ethoxycarbonylmethyl-2-chloroacetanilide, 2,3,6-trimethyl-N- (1-pyrazolylmethyl) -2-chloroacetanilide, 2, 3-dimethyl-N-isopropyl-2-chloroacetanilide, 2,6-diethyl-N- (2-n-propoxyethyl) -2-chloroacetanilide, 2- (2-methyl-4-chlorophenoxy) -N-methoxyacetamide, 2- {α-naphthoxy) -N, N-diethylpropionamide, 2,2-diphenyl-N, N-dimethylacetamide, α- (3,4,5-tribromo-1-pyrazolyl) -N, N-dimethylpropionamide , N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide, N-1-naphthylphthalamide, propionic acid 3,4-dichloroanilide, cyclopropanecarboxylic acid 3,4-dichloroanilide, acid 3,4-dichloroanilide methacrylic acid, cyclopropanecarboxylic acid 3,4-dichloroanilide, methacrylic acid 3,4-dichloroanilide, 2-methylpentanecarboxylic acid 3,4-dichloroanilide, 5-aceto mido-2,4-dimethyltrifluoromethanesulfonanilide, 5-acetamido-4-methyltrifluoromethanesulfonanilide, 2-propionylamino-4-methyl-5-chlorothiazole, N-ethoxymethyl-2,6-dimethylanilide 0- (methylsulfonyl,) O- (methylaminosulfonyl) -glycolic acid N-isopropylanilide, O- (isopropylamino-sulfonyl) -glycolic acid N-isopropylanilide, O- (methylaminosulfonyl) -glycolic acid N-isopropylanilide, 2,6-dichlorothiobenzamide, dichlorothiobenzamide, 2,6-dichlorobenzonitrile, 3,5-dibromo-4-hydroxybenzonitrile and the salts, 3, 5-diiodo-4-hydroxybenzonitrile, and the 3,5-dibromo-4-hydroxy-0-2,4-dinitrophenyl- salts benzaldoxime and salts, 3,5-dibromo-4-hydroxy-0-2-cyano-4-nitrophenylbenzaldoxime and salts, sodium pentachlorophenate, 2,4-dichlorophenyl-4'-nitrophenylether, 2,4,6-trichlorophenyl- 4'-nitrophenylether, 2-fluoro-4,5-dichlorophenyl-4'-nitrophenylether, 2-chloro-4-trifluoromethylphenyl-4'-nitrophenyl ether, 2,4'-dinitro-4-trifluoromethyl diphenylether, 2,4-dichlorophenyl -3'-methoxy -4'-nitrophenyl ether, 2,4-Chloro-4-trifluoromethylphenyl-3 / -ethoxy-4'-nitrophenylether, 2-chloro-4-trifluoromethylphenyl-3'-carboxy-4'-nitrophenylether and salts, 2,4 -dichlorophenyl-3'-methoxycarbonyl-4'-nitrophenylether, 2- (3,4-dichlorophenyl) -4-methyl-1,2,4-oxadiazolidine-3,5-dione, 2- (3-tert- butylcarbamoyloxyphenyl) -4-methyl- 1-oxadiazolidine- 3S-dione, 2- (3-isopropylcarbamoyloxyphenyl) -4-methyl-1,2,4-oxadiazolidine-3,5-dione, 2-phenyl-3,1 -benzoxazin-4-one, (4-bromophenyl) -3,4,5,9,10-pentaazatetracyclo- (5,4,1,0t8; 0.8'11) dodeca-3.9- * diene, methanesulfonate 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl, 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl dimethylaminosulfate, N-methyl-N- 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl, 3,4-dichloro-1,2-benzisothiazole, N-4-chlorophenylsuccinimide, 2-methyl-4,6 acetylaminosulfonate, 2-methyl-4,6 -dunitrophenol and salts and esters, 15 2-sec-butyl-4,6-dinitrophenol and salts, 2-sec-butyl-4 acetate , 6-dinitrophenol, 2-tert-butyl-4,6-dinitrophenol acetate, 2-tert-butyl-4,6-dinitrophenol and salts, 2-tert-butyl-5-methyl-4,6-dinitrophenol and 20 39 35 salts, 2-tert-butyl-5-methyl-4,6-dinitrophenol acetate, 2-sec-amyl-4,6-dinitrophenol, and salts and esters, 1- (a, a-dimethylbenzyl) -3 - (4-methylphenyl) urea, 1-phenyl-3- (2-methylcyclohexyl) -urea, 1-phenyl-1-benzoyl-3,3-dimethylurea, 1- (4-chlorophenyl) -1-benzoyl-3 , 3-dimethylurea, 1- (4-chlorophenyl) -3,3-dimethylurea, 1- (4-chlorophenyl) -3-methyl-3-but-1-yn-3-yl-urea, 1- ( 3,4-dichlorophenyl) -3,3-dimethylmeter, 1- (3,4-dichlorophenyl) -1-benzoyl-3,3-dimethylurea, 1- (3,4-dichlorophenyl) -3-methyl-3 -n-butylurea, 1- (4-isopropylphenyl) -3,3-dimethylurea, 1- (3-trifluoromethylphenyl) -3,3-dimethylurea, 1- (3-a, a, 0, p-tetrafluoroethoxyphenyl) ) -3,3-dimethylurea, 1- (3-tert-butylcarbamoyloxyphenyl) -3,3-dimethylurea, 1- (3-chloro-4-methylphenyl) -3,3-dimethylurea, l - (3-cWoro- 4-methoxyphenyl) -3,3-dimethylurea, 1- (3,5-dichloro-4-methoxyphenyl) -3,3-dimethylurea, 50 1- (4- (4'-chlorophenoxy) -phenyl) -3,3-dimethylurea, 1- / 4- (4'-methoxyphenoxy) -phenyl / -3,3-dimethylurea, 1-cyclooctyl-3,3-dimethylurea, 1- (hexa-hydro 4,7-metanoindan-5-lyo) -3,3-dimethylurea, 1- / 1- or 2- (3a, 4,5,7,7a-hexahydro) -4,7-methaninanenyl) - 3,3-dimethylurea, 1- (4-fluorophenyl) -3-carboxymethoxy-3-methyl-eo urea, 1-phenyl-3-methyl-3-methoxyurea, 1- (4-chlorophenyl) -3-methyl-3 -methoxycarbamide, 1- (4-bromophenyl) -3-methyl-3-methoxyurea, 1- (3,4-dichlorophenyl) -3-methyl-3-methoxy urea, 126 256 19 2t 1- (3-chloro -4-bromophenyl) -3-methyl-3-methoxyurea, 1- (3-chloro-4-isopropylphenyl) -3-methyl-3-methoxyphenyl), 1- (3-chloro-4-methoxyphenyl) -3-methyl-3-methoxyurea, 1- (3-tert-butylphenyl) -3-methyl-3-methoxyurea, 1- (2-benzothiazolyl) -1,3-dimethylurea, 1- (2- benzothiazolyl) -3-methylurea, 1- (5-trifluoromethyl-1,3,4-thiadiaz olyl) -1,3-dimethylurea, 2-imidazolidinone-1-carboxylic acid isobutylamide, 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate, 1,2,4-trimethyl-3,5 methyl sulfate 1,2-dimethyl-4-bromo-3,5-diphenylpyrazolium, 1,3-dimethyl-4- (3,4-dichlorobenzoyl) -5- / (4-methylphenyl) -difeinl-benzoyl methylsulfate -sufonyloxy) -pyrazole, 2,3,5-trichloro-4-pyridinol, 1-methyl-3-phenyl-5- (3'-trifluoromethylphenyl) -4-pyridone, 1-methyl-4-phenylpyridinium chloride, 1,1-dimethylpyridinium chloride, 3-phenyl-4-hydroxy-6-chloropyridazine, 1,1'-dimethyl-4,4'-dimethylsulfate, 1,1'-di- (3 , 5-dimethylmorpholinocarbonylmethyl) -4,4'-dipyridyl, 1,1'-ethylene-2,2'-dipyridyl dibromide, 3- (1- (N-ethQxyamino) -propylidene) -6-ethyl-3, 4-dihydro-2H-pyran-2,4-dione, 3- (1- (N-allyloxyamino) -propylidene) -6-ethyl-3,4-dihydro-2H-pyran-2,4-dione, 2- / 1- (N-allyloxyamino) -propylidene / -5,5-dimethyl-1,3-cyclohexanedione and salts, 2- / 1- (N-allylox yamino) -butylidene / -5,5-dimethyl-1,3-cyclohexanedione and salts, 2- (1- (N-allyloxyamino) -butylidene) -5,5-dimethyl-4-methoxycarbonyl-1, 3-cyclohexanedione and salts, 2-chlorophenoxyacetic acid and salts, esters and amides, 4-chlorophenoxyacetic acid and salts, esters and amides, 2,4-dichlorophenoxyacetic acid and salts, esters and amides, 2,4,5-trichlorophenoxyacetic acid and salts, esters and amides, 2-methyl-4-chlorophenoxyacetic acid and salts, esters and amides, 3,5,6-trichloro-2-pyridinoloxyacetic acid and salts, esters and amides, methyl α-naphthoxyacetic acid, 2- (2 -methylphenkox) - propionic and salts, esters and amides, 2- (4-chlorophenoxy) -propionic acid and salts, esters and amides, 2- (2,4-dichlorophenoxy) -propionic acid and salts, esters and amides, 2 acid - (2-methyl-4-chlorophenoxy) -propionic acid and salts, esters and amides, 4- (2,4-dichlorophenoxy) -butyric acid and salts, esters and amides, 4- (2-methyl-4-chlorophenoxy) acid -butyric acid and salts, esters and amides, cyclohexyl-3- (2,4-dichlorophenoxy) -acrylate, acid 9- hydroxyfluorene-9-carboxylic acid and salts and esters, 2,3,6-trichlorophenylacetic acid and salts and esters, 4-chloro-2-oxo-3-benzothiazolinylacetic acid and salts and esters, gibeleric acid and salts, di-sodium methyl aroxonate, monosodium methylarsonate, N-phosphonomethylglycine and N, N-bis-phosphonomethyl-glycine salts and salts, 2-chloroethyl 2-chloroethanophosphonate, ammonium ethylcarbamoylphosphonate, di-n-butyl-1-n-butylaminocyclohexylphosphorylphosphate , Diisopropyl 5- (2-benzosulfonylamino-ethyl) -phosphorodithioate, 2,3-dihydro-5,6-dimethyl-1,4-dithiin, 1,1,4,4-tetroxide, 5-tert-butyl-3- ( 2,4-dichloro-5-isopropoxyphenyl) -1,3,4-oxadiazol-2-one, 4,5-dichloro-2-trifluoromethylbenzimidazole and salts, 1,2,3,6-tetrahydro-3,6 -pyridazedione and succinic acid mono-N-dimethylhydrazide and salts, (2-chloroethyl) -trimethylamino chloride, (2-methyl-4-phenylsulfonyl-trifluoromethanesulfonanilide, 1,1-dimethyl-4,6-diisopropyl) -5-indanylethylloketo n, sodium chlorate, ammonium thiocyanate, calcium cyanamide, 2-chloro-4-trifluoromethylphenyl-3'-ethoxycarbonyl-4'-nitrophenylether, 1- (4-benzyloxyphenyl) -3-methyl-3-methoxyurea , 2- / 1- (2,5-dimethylphenyl) -ethylsulfonyl) -pyridine N-oxide, 1-acetyl-3-anilino-4-methoxycarbonyl-5-methylpyrazole, 3-anilino-4-methoxycarbonyl- 5-methylpyrazole, 3-tert-butylamino-4-methoxycarbonyl-5-methylpyrazole, N-benzyl-N-isopropyltrimethylacetamide, methyl 2- (4- (4'-chlorophenoxymethyl) phenoxy) propionate, 2- / 4 Ethyl - (5'-bromopyridyl-2-oxy) -phenoxy) -propionate, ethyl 2- (4- (5'-iodopyridyl-2-oxy) -phenoxy) -propionate, 2- (4- (5'-iodopyridyl) N-butyl -2-oxy) -phenoxy / -propionate, 2-chloro-4-trifluoromethylphenyl-3 '- (2-fluoroethoxy) -4'-nitrophenylether, 2-chloro-4-trifluoromethylphenyl-3'-ethoxycar - bonylmethylthio-4'-nitrophenylether, 2,4,6-trichlorophenyl-S'-ethoxycarbonyiomethylthio-4'-nitrophenylether, 2- (MN-ethoxyamino) -butylidene / -5- (2-ethylthiopropyl) -3 -hydroxy-2-cyclohexene- l-one and salts, 2- (l- (N-ethoxyamino) -butylidene) -5- (2-phenylthiopropyl) -3-hydroxy-2-cyclohexen-l-one and salts, 10 15 20 25 30 35 40 45 50 53 60126 256 tl 22 ethyl 4- (4- (4'-trifluoromethyl) -phenoxy) -pentene-2-carboxylate, 2-chloro-4-trifluoromethylphenyl-3'-methoxycarbonyl-4'- nitrophenylether, 2,4-dichlorophenylp-3'-carboxy-4'-nitrophenylether and salts, 4,5-dimethoxy-2- (3-a, a, p-trifluoro-p-bromoethoxyphenyl) -32H-pyridazinone, 2,4-dichlorophenyl-3'-ethoxyethoxyethoxy-4'-nitrophenylether, 2,3-dihydro-3,3-dimethyl-5-benzofuranyl ethanesulfonate, N- (4-methoxy-6-methyl-1,3, mriazine Ethyl 2-ylamino-carbonyl) -2-chlorobenzenesonamide, 1- (3-chloro-4-ethoxyphenyl) -3,3-dimethylurea, ethyl 2-methyl-4-chlorophenoxythioacetate is also advantageous. alone or in combination with other herbicides with still further plant protection agents, for example with plant protection agents, for example with pest control agents disease-causing plants, fungi or bacteria. Moreover, interesting are the mixtures of the agent according to the invention with solutions of mineral salts which are used to compensate for a nutrient or micronutrient deficiency. Optionally, non-toxic to plants oils and oily concentrates are also added. The compositions according to the invention are used, for example, in the form of solutions, powders, suspensions or dispersions suitable for direct spraying, emulsions, oil dispersions, pastes, and dusts. pouring, sprinkling or granulating by spraying, fogging, dusting, sprinkling or dusting. The form used depends entirely on the purpose for which it is to be used and in any case should, as far as possible, ensure the finest possible distribution of the active substance. In order to prepare solutions, emulsions, pastes and oil dispersions suitable for direct spraying, fractions are used. mineral oil with a medium to high boiling point, such as kerosene or diesel engine oil, also oils of coal tar etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example gasoline zen, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, for example methanol, ethanol, propanol, butaol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophrone etc., highly polar solvents , e.g. dimethylformamide, dimethylsulfoxide, N-methylpyrrolion, water, etc. - Aqueous use forms are prepared by adding water to the concentrate In order to prepare emulsions, pastes or oil dispersions, the active substances as such or dissolved in oil or solvents are homogenized in water with wetting agents, adhesion promoters, dispersants or emulsifiers. guys. It is also possible to prepare concentrates suitable for the dilution of water, consisting of active ingredient, wetting agent, adhesion promoter, dispersant or emulsifier and optionally a solvent or an oil. As surfactants, alkali metal salts, alkaline earth metal salts 5 and ammonium salts of lignin sulfonic acid can be used. , naphthalenesulfonic acids and phenolsulfonic acid, alkylarylsulfonates, alkyl sulfates, alkanesulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, sulfated ethoxylated lauryl alcohol, sulfates of fatty alcohols, alkali metal and alkali metal salts of alkali metals salts, salts of sulfated hexadecanols, heptecanols and octadecanols, salts of sulfated glycol ether and fatty alcohol, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or no naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol nonylphenol, polyglycol alkylphenol ethers, polyglycol tributylphenyl ether, polyglycol alkyl aryl ether alcohols, ethoxylated alcohol ethoxylates, isotridyl alcohol ethoxylates Castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, polyglycol lauryl acetal ether, sobrit esters, lignin, sulfite lugs and methylcellulose. Powders, dusting and dusting agents are prepared by mixing or grinding together. of the active ingredients with a solid carrier. Granules, for example coated granules, impregnated and homogeneous, are prepared by combining the active ingredients with solid carriers. Suitable solid carriers are, for example, mineral earths such as silicic acids, silicates, talc, kaolin, lime, clay bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics. artificial fertilizers, such as, for example, ammonium sulphates, ammonium phosphate, ammonium nitrate, ureas, and plant products such as cereal flour, wood-bark, wood and nut flour, powdered cellulose and other solid carriers. Examples of the preparation of active compound preparations are given below. Example VIII. 90 parts by weight of active ingredient No. 1 are mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solution is obtained which is suitable for use in the form of very fine drops. Example IX. 20 parts by weight of the active ingredient No. 2 are dissolved in a mixture of 80 parts by weight of xylene, 10 parts by weight of 5 parts by weight of 8-10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 by weight of dodecylbenzenesulfonic acid calcium salt and 5 parts by weight of the product of the addition of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient. Example X 20 parts by weight of the ingredient of active ingredient No. 3 are dissolved in a mixture consisting of 126 256 23 24 40 parts by weight cyclohexanes !, 30 parts by weight of isobutanol, 20 parts by weight of the additive product, 7 moles of ethylene oxide with 1 mole of isoctylphenol, and 10 parts by weight of the product of the addition of 40 moles of ethylene oxide to 1 mole of tin oil. By pouring the solution into 100,000 parts by weight of water and thoroughly mixing it, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient. Example XI. 20 parts by weight of active ingredient No. 4 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction with a boiling point of 210-280 ° C and 10 parts by weight of the product of adding 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0) 02% by weight of the active ingredient. Example XII. 20 parts by weight of the active ingredient No. 1 is thoroughly mixed and ground in a hammer mill with 3 parts by weight of sodium diisobutylnaphthalene-a-surfonic acid, 17 parts by weight of sodium ligninsulfonic acid from the sulfite hatch and 60 parts by weight of powdered gel. Silica. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained, containing 0.1% by weight of active sbustance, Example XIII. 3 parts by weight of active ingredient No. 2 is mixed thoroughly with 97 parts by weight of finely powdered kaolin. This gives a dust with 3% by weight of active ingredient. Example XIV. 30 parts by weight of Active Ingredient No. 3 are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of the gel. This gives an active compound formulation with good adhesion. XV. 40 parts by weight of active ingredient No. 4 is mixed with exactly 10 parts of sodium phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. Thus a stable aqueous dispersion is obtained, by diluting with 100,000 parts by weight of water an aqueous dispersion is obtained containing 0.04% by weight of the active ingredient. Example XVI. 20 parts of the active ingredient No. 1 are mixed with 12 parts of calcium dodecylbenzene sulphonic acid, 8 parts of fatty alcohol and polyglycol ether, 2 parts of sodium phenolsulphonic acid-urea-formaldehyde condensate and 68 parts of paraffinated acid. mineral oil. In this way, a stable oil dispersion is obtained. In the greenhouse selective herbicide test, with the post-emergence application of an active ingredient dose of 0.25 kg / hectare, the new active ingredient no. 4 shows a better selective herbicidal action than the known active ingredient A. 5 In the selective control of weeds in a greenhouse with a post-emergence application of an active ingredient dose of 0.5 kg / hectare, the new active ingredient No. 88 has a better selective herbicidal action than the known active ingredient B. 10 In a greenhouse herbicidal study with pre-emergence application an active compound dose of 3 kg / hectare, the new active compounds Nos. 4 and 88 show very good herbicidal activity. In a greenhouse herbicidal study with 0.25 kg / hectare of active ingredient post-emergence, the new active ingredient No. 88 shows a better selective herbicidal action than the known active ingredient B. 20 In the herbicidal study in In the case of the post-emergence application of the active ingredient in doses of 0.5 and 0.25 kg / hectare, the new active compounds Nos. 7 and 102 show a better selective herbicidal action than the known active ingredient CW in a greenhouse herbicidal test. In addition to the post-emergence application of an active sustenance of 0.5 kg / hectare, active compounds Nos. 87 and 126 show good herbicidal activity. In a study of the herbicidal effectiveness in a greenhouse with the post-emergence application of active compound at a rate of 0.25 kg / hectare, active compounds Nos. 22 and 101 show a good herbicidal action. 33 Patent claim A herbicide comprising a solid or liquid carrier and an active ingredient, characterized in that the active ingredient is pyridazone under general formula I, in which R2 is a halogen atom or an alkoxy group with 1-3 carbon atoms, Ri is amino groups , alkylamino, dialkylamino, alkoxyamino or alkylalkoxyamino, containing 1-3 carbon atoms each in the alkyl or alkoxy group, the alkyl groups being the same or different, hereinafter R1 is a halogen atom, an alkoxy group of 1-3 carbon atoms, a trimethyleneimine group or an amino group acylated by an M group of formula C1CH2C (O) or CH, COOCH, C (O), X represents a substituted phenoxy group of general formula 2, where R3, R4 and R5 each independently represent a hydrogen or halogen atom, a nitro, cyano, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxyl, alkyl mercaptan, haloalkylomer groups. - captan, alkylsulfinyl or alkylsulfonyl with 1 to 4 carbon atoms in each case and Y is hydrogen, cyano, haloalkyl, halogen or nitro. 126 256 Cl NaOCHj-NaCl ° xx CF3 OCH3 'xr CE SCHEME -0- \ \ & <• or CHIP u PATTERN 5 Hal PATTERN 6 NHNH2 NH2 W20R 7 PATTERN 8 PL

Claims (1)

1. Patent claim A herbicide containing a solid or liquid carrier and an active ingredient, characterized in that the active ingredient is pyridazone under the general formula I, in which R2 is a halogen atom or an alkoxy group with 1-3 carbon atoms, Ri represents the groups amine, alkylamino, dialkylamino, alkoxyamino or alkylalkoxyamino, containing 1 to 3 carbon atoms each time in the alkyl or alkoxy group, the alkyl groups being the same or different, hereinafter R 1 is a halogen atom, an alkoxy group with 1 - 3 carbon atoms, a trimethyleneimino group or an amino group acylated by an M group of formula C1CH2C (O) or CH, COOCH, C (O), X represents a substituted phenoxy group of general formula 2, where R3, R4 and R5 each independently represent a hydrogen or halogen atom, a nitro, cyano, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxyl, alkylmercaptan, haloalkylomer groups - captan, alkylsulfinyl or alkylsulfonyl with 1 to 4 carbon atoms in each case and Y is hydrogen, cyano, haloalkyl, halogen or nitro. 126 256 Cl NaOCHj-NaCl ° xx CF3 OCH3 'xr CE SCHEME -0- \ \ & <• or CHIP u PATTERN 5 Hal PATTERN 6 NHNH2 NH2 W20R 7 PATTERN 8 PL